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Título: | Iron-Catalyzed Prins-Peterson Reaction for the Direct Synthesis of δ4-2,7-Disubstituted Oxepenes |
Autor: | Cruz, Daniel A. CSIC ORCID; Sinka, Victoria CSIC ORCID; Martín, Víctor S. CSIC ORCID; Padrón, Juan I. CSIC ORCID | Palabras clave: | Oxepenes Synthesis |
Fecha de publicación: | 25-sep-2018 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 83: 12632-12647 (2018) | Resumen: | A direct iron(III)-catalyzed Prins-Peterson reaction involving α-substituted γ-triphenylsilyl bis-homoallylic alcohols and aldehydes is described. Thus, cis--2,7-disubstituted oxepenes were synthesized in a diastereoselective reaction using sustainable catalytic conditions (3-5 mol %). This highly productive process is the result of a cascade of three chemical events with the concomitant formation of a C-O bond, a C-C bond, and a endocyclic double bond, through a Prins cyclization followed by a Peterson-type elimination. This tandem reaction is chemoselective vs the classical Prins cyclization. | Versión del editor: | https://doi.org/10.1021/acs.joc.8b01978 | URI: | http://hdl.handle.net/10261/179831 | DOI: | 10.1021/acs.joc.8b01978 | Identificadores: | doi: 10.1021/acs.joc.8b01978 e-issn: 1520-6904 issn: 0022-3263 |
Aparece en las colecciones: | (IPNA) Artículos |
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Iron-Catalyzed Prins-Peterson_JIPadron_JOC18 .pdf | 1,38 MB | Adobe PDF | Visualizar/Abrir |
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